CA2243306C - Solubilized hydrophobically-modified alkali-soluble emulsion polymers - Google Patents

Solubilized hydrophobically-modified alkali-soluble emulsion polymers Download PDF

Info

Publication number: CA2243306C
Authority: CA; Canada
Prior art keywords: weight; cyclodextrin; polymer; hase; modified alkali
Prior art date: 1997-07-29
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA002243306A

Other languages

English (en)

French (fr)

Other versions

CA2243306A1 (en

Inventor

Gary David Greenblatt

Willie Lau

Andrew Gordon Batzell Iii

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Rohm and Haas Co

Original Assignee

Rohm and Haas Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-07-29

Filing date

1998-07-16

Publication date

2003-03-11

1998-07-16 Application filed by Rohm and Haas Co filed Critical Rohm and Haas Co

1999-01-29 Publication of CA2243306A1 publication Critical patent/CA2243306A1/en

2003-03-11 Application granted granted Critical

2003-03-11 Publication of CA2243306C publication Critical patent/CA2243306C/en

2018-07-16 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000004908 Emulsion polymer Substances 0.000 title claims abstract description 9
239000007864 aqueous solution Substances 0.000 claims abstract description 9
229920000642 polymer Polymers 0.000 claims description 59
239000000178 monomer Substances 0.000 claims description 33
239000000203 mixture Substances 0.000 claims description 17
239000007787 solid Substances 0.000 claims description 15
230000002209 hydrophobic effect Effects 0.000 claims description 13
-1 triacetyl Chemical group 0.000 claims description 11
239000000839 emulsion Substances 0.000 claims description 10
239000004094 surface-active agent Substances 0.000 claims description 10
229920000858 Cyclodextrin Polymers 0.000 claims description 9
238000000034 method Methods 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
150000002894 organic compounds Chemical class 0.000 claims description 8
235000019333 sodium laurylsulphate Nutrition 0.000 claims description 7
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 6
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 5
HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 claims description 5
238000007865 diluting Methods 0.000 claims description 3
WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims 2
125000000129 anionic group Chemical group 0.000 claims 1
GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 claims 1
230000003472 neutralizing effect Effects 0.000 claims 1
230000000379 polymerizing effect Effects 0.000 claims 1
239000000243 solution Substances 0.000 abstract description 16
241000283986 Lepus Species 0.000 description 42
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 12
239000002253 acid Substances 0.000 description 9
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 7
239000002585 base Substances 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
150000001252 acrylic acid derivatives Chemical class 0.000 description 4
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 4
LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 3
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 2
IRLPACMLTUPBCL-KQYNXXCUSA-N 5'-adenylyl sulfate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](O)[C@H]1O IRLPACMLTUPBCL-KQYNXXCUSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
229920002125 Sokalan® Polymers 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000004927 clay Substances 0.000 description 2
230000007423 decrease Effects 0.000 description 2
ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
239000003999 initiator Substances 0.000 description 2
239000004816 latex Substances 0.000 description 2
229920000126 latex Polymers 0.000 description 2
239000007788 liquid Substances 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical class [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
UTOVMEACOLCUCK-SNAWJCMRSA-N (e)-4-butoxy-4-oxobut-2-enoic acid Chemical compound CCCCOC(=O)\C=C\C(O)=O UTOVMEACOLCUCK-SNAWJCMRSA-N 0.000 description 1
KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical group COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 1
CEBRPXLXYCFYGU-UHFFFAOYSA-N 3-methylbut-1-enylbenzene Chemical compound CC(C)C=CC1=CC=CC=C1 CEBRPXLXYCFYGU-UHFFFAOYSA-N 0.000 description 1
DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
229920008128 Ameripol Polymers 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
WIVTXBIFTLNVCZ-UHFFFAOYSA-N CC(=C)C(=O)OCCP(=O)=O Chemical compound CC(=C)C(=O)OCCP(=O)=O WIVTXBIFTLNVCZ-UHFFFAOYSA-N 0.000 description 1
239000004641 Diallyl-phthalate Substances 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
241001527806 Iti Species 0.000 description 1
YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
101100345589 Mus musculus Mical1 gene Proteins 0.000 description 1
101150050192 PIGM gene Proteins 0.000 description 1
240000005428 Pistacia lentiscus Species 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
229920013625 Synpol Polymers 0.000 description 1
DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004848 alkoxyethyl group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
MGFFVSDRCRVHLC-UHFFFAOYSA-N butyl 3-sulfanylpropanoate Chemical compound CCCCOC(=O)CCS MGFFVSDRCRVHLC-UHFFFAOYSA-N 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
239000012986 chain transfer agent Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
239000003599 detergent Substances 0.000 description 1
125000004386 diacrylate group Chemical group 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000004815 dispersion polymer Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 description 1
PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
NTPXNEQCDPWJQA-AZDHXYLBSA-N hydia Chemical compound C1[C@@H](O)[C@@](N)(C(O)=O)[C@@H]2[C@@H](C(O)=O)[C@H]12 NTPXNEQCDPWJQA-AZDHXYLBSA-N 0.000 description 1
150000002432 hydroperoxides Chemical class 0.000 description 1
125000001165 hydrophobic group Chemical group 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
239000000976 ink Substances 0.000 description 1
229910001869 inorganic persulfate Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
LDTLDBDUBGAEDT-UHFFFAOYSA-N methyl 3-sulfanylpropanoate Chemical compound COC(=O)CCS LDTLDBDUBGAEDT-UHFFFAOYSA-N 0.000 description 1
NKHAVTQWNUWKEO-NSCUHMNNSA-N monomethyl fumarate Chemical compound COC(=O)\C=C\C(O)=O NKHAVTQWNUWKEO-NSCUHMNNSA-N 0.000 description 1
229940005650 monomethyl fumarate Drugs 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000004745 nonwoven fabric Substances 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
239000003973 paint Substances 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
239000004597 plastic additive Substances 0.000 description 1
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 1
238000003756 stirring Methods 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
229940096522 trimethylolpropane triacrylate Drugs 0.000 description 1
238000000108 ultra-filtration Methods 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/062—Copolymers with monomers not covered by C09D133/06
- C09D133/064—Copolymers with monomers not covered by C09D133/06 containing anhydride, COOH or COOM groups, with M being metal or onium-cation

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Polymers & Plastics (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Materials Engineering (AREA)
Wood Science & Technology (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Compositions Of Macromolecular Compounds (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Polymerisation Methods In General (AREA)
Paints Or Removers (AREA)
Processes Of Treating Macromolecular Substances (AREA)

CA002243306A 1997-07-29 1998-07-16 Solubilized hydrophobically-modified alkali-soluble emulsion polymers Expired - Fee Related CA2243306C (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US5383297P	1997-07-29	1997-07-29
US60/053,832		1997-07-29

Publications (2)

Publication Number	Publication Date
CA2243306A1 CA2243306A1 (en)	1999-01-29
CA2243306C true CA2243306C (en)	2003-03-11

Family

ID=21986842

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002243306A Expired - Fee Related CA2243306C (en)	1997-07-29	1998-07-16	Solubilized hydrophobically-modified alkali-soluble emulsion polymers

Country Status (13)

Country	Link
US (1)	US6063857A (id)
EP (1)	EP0896027B1 (id)
JP (1)	JPH11152411A (id)
KR (1)	KR100590815B1 (id)
CN (1)	CN1165576C (id)
AU (1)	AU749553B2 (id)
BR (1)	BR9802609A (id)
CA (1)	CA2243306C (id)
DE (1)	DE69800268T2 (id)
ID (1)	ID20646A (id)
MX (1)	MX200986B (id)
NZ (1)	NZ331019A (id)
TH (1)	TH34258A (id)

Families Citing this family (54)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU4969199A (en)	1998-07-10	2000-02-01	S.C. Johnson Commercial Markets, Inc.	Continuous bulk polymerization and esterification process and compositions including the polymeric product
WO2000002932A1 (en)	1998-07-10	2000-01-20	S. C. Johnson Commercial Markets, Inc.	Process for producing polymers by free radical polymerization and condensation reaction, and apparatus and products related thereto
ES2340174T3 (es)	1999-07-14	2010-05-31	Basf Corporation	Proceso para la produccion continua de polimeros de epoxi-(met)acrilico estireno y su uso en recubrimientos.
US6683129B1 (en) *	2000-03-31	2004-01-27	National Starch And Chemical Investment Holding Corporation	Salt sensitive aqueous emulsions
US6605681B1 (en)	2000-07-12	2003-08-12	Johnson Polymer, Inc.	Process for the continuous production of epoxylated addition polymers, and powder and liquid coating applications containing epoxylated addition polymers
JP2004517980A (ja)	2000-09-21	2004-06-17	ローム　アンド　ハース　カンパニー	極性モノマーと多価カチオンとに関わる方法および組成物
US20030008591A1 (en) *	2001-06-18	2003-01-09	Parsons John C.	Water dispersible, salt sensitive nonwoven materials
US7063895B2 (en) *	2001-08-01	2006-06-20	National Starch And Chemical Investment Holding Corporation	Hydrophobically modified solution polymers and their use in surface protecting formulations
KR20030027150A (ko) *	2001-09-13	2003-04-07	삼원금속 주식회사	귀금속 폐석고 탈수기
US7153496B2 (en) *	2002-01-18	2006-12-26	Noveon Ip Holdings Corp.	Hair setting compositions, polymers and methods
US7288616B2 (en) *	2002-01-18	2007-10-30	Lubrizol Advanced Materials, Inc.	Multi-purpose polymers, methods and compositions
AU2003200070B2 (en) *	2002-01-25	2008-01-24	Rohm And Haas Company	Triggered response compositions
CA2435735C (en) *	2002-07-31	2008-10-14	Rohm And Haas Company	Triggered response compositions
US20050032995A1 (en) *	2003-08-08	2005-02-10	Kulkarni Mohan Gopalkrishna	Inclusion complexes of cyclic macromolecular organic compounds and polymerization thereof
KR100694861B1 (ko) *	2004-08-25	2007-03-14	롬 앤드 하아스 컴패니	고-ｐＨ 수성 시스템용 증점제
EP1828255A1 (en) *	2004-10-29	2007-09-05	Council Of Scientific And Industrial Research	Water soluble polymers containing vinyl unsaturation, their crosslinking and process for preparation thereof
US7531591B2 (en) *	2004-12-09	2009-05-12	Hercules Incorporated	Aqueous dispersion of poly(acetal-polyether) and its use in protective coatings
US7320831B2 (en) *	2005-05-03	2008-01-22	Celanese International Corporation	Salt-sensitive vinyl acetate binder compositions and fibrous article incorporating same
US7329705B2 (en)	2005-05-03	2008-02-12	Celanese International Corporation	Salt-sensitive binder compositions with N-alkyl acrylamide and fibrous articles incorporating same
US7989545B2 (en)	2006-01-25	2011-08-02	Celanese International Corporations	Salt-sensitive binders for nonwoven webs and method of making same
JP5122215B2 (ja) *	2006-08-31	2013-01-16	ロームアンドハースカンパニー	調整された粘度を有する水性両親媒性コポリマーエマルジョンおよびその製造方法
EP1923504A1 (en) *	2006-11-20	2008-05-21	Rohm and Haas France SAS	Coated paper and paperboard
US20080224087A1 (en) *	2007-03-14	2008-09-18	Ezell Ryan G	Aqueous-Based Insulating Fluids and Related Methods
US7741401B2 (en) *	2007-03-21	2010-06-22	Rohm And Haas Company	Thickener blend composition and method for thickening aqueous systems
US20090123773A1 (en) *	2007-11-14	2009-05-14	Rajeev Farwaha	Salt-sensitive binders containing vinyl acetate for nonwoven webs and method of making same
CN101959904A (zh) *	2008-03-03	2011-01-26	国际人造丝公司	用于非织造纤网的盐敏性阳离子聚合物粘结剂及其制造方法
EP2248510A1 (en) *	2009-05-07	2010-11-10	Rohm and Haas Company	Thickened aqueous composition
WO2011062805A1 (en) *	2009-11-23	2011-05-26	Lubrizol Advanced Materials, Inc.	Surfactant-polymer blends
CN102858883B (zh) *	2010-02-12	2015-09-09	罗地亚管理公司	流变改进剂组合物及其使用方法
EP2387988B1 (en)	2010-05-19	2017-09-27	The Procter & Gamble Company	Oxidizing composition for the treatment of keratin fibres
FR2961815B1 (fr) *	2010-06-25	2013-05-10	Coatex Sas	Emulsions acryliques alkali gonflables a l'acide acrylique, leur utilisation dans des formulations aqueuses et formulations les contenant.
FR2961816B1 (fr) *	2010-06-25	2012-07-06	Coatex Sas	Emulsions acryliques alkali gonflables sans tensio-actif, leur utilisation dans des formulations aqueuses et formulations les contenant.
FR2972370B1 (fr) *	2011-03-07	2013-03-01	Coatex Sas	Procede d'epaississement d'une formulation cosmetique a partir d'une emulsion alkali gonflable d'un polymere a l'amps et riche en acide acrylique.
JPWO2012160933A1 (ja) *	2011-05-24	2014-07-31	住友精化株式会社	（メタ）アクリル酸系共重合体
EP2532689A1 (de) *	2011-06-07	2012-12-12	Basf Se	Herstellung von Polyacrylaten durch Emulsionspolymerisation
EP2712898B1 (en) *	2012-09-28	2014-11-26	Rohm and Haas Company	Hydrophobically modified alkali soluble emulsion composition with polymeric beads
ES2600159T3 (es) *	2012-11-29	2017-02-07	Unilever N.V.	Líquidos detergentes acuosos espesados
CN104968771B (zh) *	2012-11-29	2019-03-01	荷兰联合利华有限公司	聚合物结构化的水性洗涤剂组合物
CN105102525B (zh) *	2013-03-13	2019-04-16	阿克佐诺贝尔化学国际公司	流变改性剂
US9708431B2 (en)	2013-08-09	2017-07-18	Dow Global Technologies Llc	Hydrophobic alkali soluble emulsion thickener
CN104513533B (zh)	2013-09-30	2018-11-06	罗门哈斯公司	Hase流变改性剂vae乳液共聚物组合物
EP2960261A1 (en) *	2014-06-23	2015-12-30	Henkel AG&Co. KGAA	Polymer system based on hydrophobically modified water soluble polymers
EP2960262A1 (en) *	2014-06-23	2015-12-30	Henkel AG&Co. KGAA	Polymer system based on hydrophobically modified water soluble polymers
EP2960255A1 (en) *	2014-06-23	2015-12-30	Henkel AG&Co. KGAA	Method of manufacturing pH responsive latexes and uses thereof
CA2962473C (en) *	2014-09-25	2021-06-29	Ucar Emulsion Systems Fze	Paint formulation and process of making thereof
EP3250666B1 (en)	2015-01-29	2018-08-22	Unilever PLC	Thickened aqueous detergent liquid
EP3133117A1 (en) *	2015-08-17	2017-02-22	Henkel AG & Co. KGaA	Water-based polymer system for labeling adhesive applications
FR3057867B1 (fr) *	2016-10-25	2018-11-02	Coatex	Preparation d'emulsion polymerique
US11376209B2 (en)	2017-11-03	2022-07-05	Conopco, Inc.	Antidandruff composition and method of use
MX391873B (es) *	2017-11-03	2025-03-21	Unilever Ip Holdings B V	Composición de champú y método de uso.
WO2019086275A1 (en) *	2017-11-03	2019-05-09	Unilever Plc	Skin cleansing composition and method of use
WO2020144060A1 (en) *	2019-01-09	2020-07-16	Unilever Plc	Shampoo composition and method of use
CN113549443B (zh) *	2021-07-23	2023-03-21	长江大学	一种生物胶压裂液稠化剂及其制备方法
CN115558343A (zh) *	2022-09-26	2023-01-03	卡本科技集团股份有限公司	一种低透水的透气型水性涂料及其制备方法

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5573747A (en) *	1978-11-27	1980-06-03	Dow Chemical Co	Liquid emulsifying polymers useful as ph sensitive viscosifier for aqueous composition
ZA797050B (en) *	1978-12-29	1981-07-29	Rohm & Haas	Methacrylic acid emulsion copolymers for thickening purposes
US4384096A (en) *	1979-08-27	1983-05-17	The Dow Chemical Company	Liquid emulsion polymers useful as pH responsive thickeners for aqueous systems
US4351754A (en) *	1979-09-17	1982-09-28	Rohm And Haas Company	Thickening agent for aqueous compositions
US4529773A (en) *	1982-03-17	1985-07-16	David Witiak	Alkali-soluble emulsion polymers in acidic surfactant compositions
CA1285685C (en) *	1985-02-04	1991-07-02	Ching-Jen Chang	Method for preparation of hydrophobe containing alkali soluble or swellable emulsion copolymers
US4703080A (en) *	1985-04-29	1987-10-27	Desoto, Inc.	Aqueous latices having improved coating rheology
GB8521492D0 (en) *	1985-08-29	1985-10-02	Shell Int Research	Preparation of diesters of alkanedioic acids
US4990373A (en) *	1989-09-29	1991-02-05	Rusmar Incorporated	Membrane-forming foam composition and method
KR910015597A (ko) *	1990-02-14	1991-09-30	원본미기재	중합체 농화제(Polymeric Thickener)
US5137571A (en) *	1990-06-05	1992-08-11	Rohm And Haas Company	Method for improving thickeners for aqueous systems
US5376709A (en) *	1993-03-12	1994-12-27	Rohm And Haas Company	Method for improving thickeners for aqueous systems
US5399618A (en) *	1993-06-28	1995-03-21	Union Carbide Chemical & Plastics Technology Corporation	Processes for preparing aqueous polymer emulsions
US5521266A (en) *	1994-10-28	1996-05-28	Rohm And Haas Company	Method for forming polymers
US5504123A (en) *	1994-12-20	1996-04-02	Union Carbide Chemicals & Plastics Technology Corporation	Dual functional cellulosic additives for latex compositions
KR0167002B1 (ko) *	1994-12-27	1999-03-20	김충세	폴리우레탄 수분산 수지의 제조방법과 이에 따른 수지가 함유된 도료 조성물
US5639841A (en) *	1995-02-28	1997-06-17	Union Carbide Chemicals & Plastics Technology Corporation	Polymers containing macromonomer mixtures
US5530056A (en) *	1995-05-03	1996-06-25	National Starch And Chemical Investment Holding Corporation	latex binders and paints which are free of volatile coalescents and freeze-thaw additives
US5686024A (en) *	1995-12-18	1997-11-11	Rhone-Poulenc Surfactants & Specialties, L.P.	Aqueous dispersion of a surface active polymer having enhanced performance properties
DE19548038A1 (de) *	1995-12-21	1997-06-26	Basf Ag	Verfahren zur Herstellung von Polymerisaten durch Emulsionspolymerisation

1998
- 1998-07-09 MX MX9805571A patent/MX200986B/es unknown
- 1998-07-15 AU AU76192/98A patent/AU749553B2/en not_active Ceased
- 1998-07-16 CA CA002243306A patent/CA2243306C/en not_active Expired - Fee Related
- 1998-07-16 NZ NZ331019A patent/NZ331019A/xx unknown
- 1998-07-17 EP EP98305722A patent/EP0896027B1/en not_active Expired - Lifetime
- 1998-07-17 DE DE69800268T patent/DE69800268T2/de not_active Expired - Lifetime
- 1998-07-20 US US09/119,500 patent/US6063857A/en not_active Expired - Lifetime
- 1998-07-23 TH TH9801002823A patent/TH34258A/th unknown
- 1998-07-24 ID IDP981045A patent/ID20646A/id unknown
- 1998-07-24 KR KR1019980029819A patent/KR100590815B1/ko not_active Expired - Fee Related
- 1998-07-27 JP JP10211191A patent/JPH11152411A/ja active Pending
- 1998-07-28 CN CNB981166342A patent/CN1165576C/zh not_active Expired - Lifetime
- 1998-07-28 BR BR9802609-7A patent/BR9802609A/pt not_active Application Discontinuation

Also Published As

Publication number	Publication date
TH34258A (th)	1999-08-06
AU7619298A (en)	1999-02-11
DE69800268T2 (de)	2001-03-15
US6063857A (en)	2000-05-16
DE69800268D1 (de)	2000-09-28
AU749553B2 (en)	2002-06-27
JPH11152411A (ja)	1999-06-08
CN1208745A (zh)	1999-02-24
CN1165576C (zh)	2004-09-08
KR19990014137A (ko)	1999-02-25
EP0896027A1 (en)	1999-02-10
KR100590815B1 (ko)	2006-10-11
NZ331019A (en)	2000-01-28
MX9805571A (en)	1999-01-31
ID20646A (id)	1999-02-04
MX200986B (en)	2001-03-07
EP0896027B1 (en)	2000-08-23
CA2243306A1 (en)	1999-01-29
BR9802609A (pt)	2000-02-08

Legal Events

Date	Code	Title	Description
1998-07-16	EEER	Examination request
2010-07-16	MKLA	Lapsed

Publication	Publication Date	Title
CA2243306C (en)	2003-03-11	Solubilized hydrophobically-modified alkali-soluble emulsion polymers
JP5015372B2 (ja)	2012-08-29	ポリマー組成物
JPH0770254A (ja)	1995-03-14	水性分散物の状態または再分散性粉末の状態のカルボキシル基含有コポリマーおよびそれの水溶性塩、それの製造方法およびそれの用途
US20060229369A1 (en)	2006-10-12	Use of 2-hydroxy-2-sulfinato acetic acid or the salts thereof as an initiator in w/o emulsions
KR100768156B1 (ko)	2007-10-17	수성 분산물의 제조방법
WO2004016658A2 (en)	2004-02-26	Dispersions containing living radicals
IL125860A (en)	2002-02-10	Method of improving the efficiency of a chain transfer agent having low water solubility